US20170066947A1 - Primer for enhancing tape adhesion to hydrophilic surfaces - Google Patents

Primer for enhancing tape adhesion to hydrophilic surfaces Download PDF

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Publication number
US20170066947A1
US20170066947A1 US15/308,136 US201515308136A US2017066947A1 US 20170066947 A1 US20170066947 A1 US 20170066947A1 US 201515308136 A US201515308136 A US 201515308136A US 2017066947 A1 US2017066947 A1 US 2017066947A1
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Prior art keywords
primer
radical
adhesion
monomer mixture
acrylate
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US15/308,136
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Inventor
Sebastian Dietze
Kai Ellringmann
Marco Kupsky
Uwe Schümann
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Tesa SE
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Tesa SE
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Assigned to TESA SE reassignment TESA SE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ELLRINGMANN, KAI, Dietze, Sebastian, KUPSKY, MARCO, Schümann, Uwe
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/05—Alcohols; Metal alcoholates
    • C08K5/057—Metal alcoholates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
    • C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J139/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Adhesives based on derivatives of such polymers
    • C09J139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J139/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Adhesives based on derivatives of such polymers
    • C09J139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • C09J139/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J7/02—
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2433/00—Presence of (meth)acrylic polymer
    • C09J2433/003—Presence of (meth)acrylic polymer in the primer coating

Definitions

  • the present invention relates to the technical field of primers for improving the adhesion of adhesive tapes to hydrophilic surfaces, such as to glass surfaces.
  • a primer composition for improving the adhesion of polyacrylate-based adhesive tapes which may comprise pigments or other functional, fillerlike substances in high concentration, without thereby substantially impairing the adhesion-promoting effect.
  • Primer compositions are disclosed in a multitude of patents, though only a few specifications describe primers whose purpose is to improve adhesion of adhesive tapes.
  • a primer composition is proposed that is based on a maleic anhydride-modified polyolefin and an organic diamine, the intention therewith being to improve adhesion to polyolefin-based materials.
  • JP 2008-156566 A discloses, for adhesive tape applications, a primer composition based on an acidic acrylate polymer and a fluorine-containing copolymer.
  • WO 02/100961 A1 proposes a primer composition which comprises an acrylate copolymer grafted with an aminoalkyl group containing terminal primary amino groups, an acrylate copolymer having carboxyl groups in the molecular chain, and a solvent.
  • WO 03/052021 A1 describes a primer composition which comprises a polydiorganosiloxane-polyurea copolymer with electron-rich groups, which may take the form of a primer, an adhesive, a pressure sensitive adhesive, or another coating material.
  • This primer composition as well is identified in connection with adhesive tape applications.
  • EP 833 865 B1, EP 833 866 B1, EP 739 383 B1 and U.S. Pat. No. 5,602,202 describe primer compositions which are based on mixtures of styrene/diene block copolymers or styrene/hydrogenated diene block copolymers and selected polyacrylates, whose aim is to improve the adhesion of double-sidedly adhesive, foamed adhesive tapes to both low-energy and higher-energy surfaces.
  • a primer which is suitable for improving the adhesion of adhesive tapes to substrates where bondability is difficult, particularly to galvanized steel, and also to thermoplastic, olefin-based elastomers such as PP/EPDM, for example, is disclosed in DE 10 2011 077 510 A1.
  • silane primers or silane adhesion promoters are described for example in DE 10 2009 007 930 A1 or in DE 10 2007 030 196 A1, and additionally in EP 577 014 A1, EP 1 693 350 A1, EP 1 730 247 A1, US 2008 0245 271 A, US 2008 023 425 A, or WO 2008/025846 A2.
  • the systems disclosed in the cited specifications are not designed for improving the adhesion of adhesive tapes to glass. Accordingly, they contain no components suitable for improving the adhesion to a pressure sensitive adhesive, more particularly the adhesion to a pressure sensitive adhesive based on a copolymer of acrylic esters and, optionally, acrylic acid.
  • U.S. Pat. No. 6,646,048 B2 discloses a primer composition composed of a reactive acrylic resin which consists of two different methacrylates, a silane compound, an epoxy resin of the bisphenol A type, and carbon black.
  • This primer composition of a reactive acrylic resin and a silane is indeed suitable for improving the adhesion of a urethane-based sealant or of a reactive adhesive to glass, but must be regarded as unsuitable for improving the adhesion of a pressure sensitive adhesive tape to glass.
  • the problem addressed by the invention is, generally, the provision of a primer for improving the adhesion of adhesive tapes to hydrophilic surfaces such as, in particular, glass or ceramic.
  • the primer here is intended preferably to allow the incorporation of pigments or other functional fillers in high concentration, without thereby significantly reducing the adhesion-promoting effect of the primer. It is to be possible to incorporate pigments into the primer at such a high concentration that opacity is achieved when this primer is applied in a thin film to glass.
  • the term “thin film” here refers to a film thickness of the order of between approximately 5 ⁇ m and 20 ⁇ m. Opaque means that it ought not to be possible to see through the primer layer, and therefore that visible light ought not to shine through the primer layer.
  • the adhesion-promoting effect of the primer is to be built up rapidly.
  • An adhesive tape adhered to the primer layer is in particular to be no longer detachable after just 24 hours from the primer layer applied to a glass or ceramic surface.
  • the primer ought to be designed in such a way that an adhesive tape can be adhered to the primer layer just a short time after the primer has been applied to the substrate surface, particularly to glass. Even shortly after application, therefore, the primer is to be “dry”, meaning that the solvent is to have evaporated after just a short time.
  • a short time here refers to a period of 60 seconds, preferably 40 seconds.
  • the primer is to be free from halogen-containing, and especially chlorine-containing, substances.
  • the subject of the invention in a first and general embodiment is a primer which comprises a mixture G which is dispersed or dissolved in one or more solvents and comprises
  • Vinylcaprolactam refers to N-vinylcaprolactam (CAS No. 2235-00-9) and “vinylpyrrolidone” refers to N-vinyl-2-pyrrolidone (CAS No. 88-12-0).
  • a metal acetylacetonate in accordance with the invention is a coordination compound composed of acetylacetonate anions and metal cations.
  • the general formula is as follows: M(acac) m .
  • M here is a metal cation
  • acac is the acetylacetonate anion.
  • the IUPAC name for acetylacetone is as follows: pentane-2,4-dione, and the CAS No. is as follows: 123-54-6.
  • m is the number of acetylacetonate anions which are necessary for charge compensation. m is dependent on the oxidation state of the metal cation.
  • metal alkoxide is a synonym for “metal alcoholate”. It relates to coordination compounds of the general formula: M(OR) n .
  • M here is a metal cation
  • OR is an alkoxide anion.
  • R is an alkyl radical.
  • n is the number of alkoxide anions which are necessary for charge compensation. n is dependent on the oxidation state of the metal cation.
  • Alkoxy-metal acetylacetonates are understood in this specification to be mixed coordination compounds composed of acetylacetonate anions and alkoxide anions and of metal cations.
  • the general formula is as follows: M(acac) m (OR) n .
  • M here is a metal cation, acac the acetylacetonate anion, and OR an alkoxide anion.
  • R is an alkyl radical.
  • m and n are the number of acetylacetonate anions and alkoxide anions, respectively, which are necessary for charge compensation. m and n are dependent on the oxidation state of the metal cation.
  • Primers of the invention exhibit strong adhesion to hydrophilic substrates such as, in particular, glass or ceramic, on the one hand, and to adhesive tapes, especially those with polar pressure sensitive adhesives, as for example with pressure sensitive adhesives based on polyacrylic esters, on the other. Accordingly, primers of the invention are excellent adhesion promoters for bonds of adhesive tapes to glass and ceramic.
  • the adhesion-promoting effect of a primer of the invention here begins very rapidly. It has been found that an adhesive tape adhered to the primer layer could no longer be detached without destruction from the primer layer applied to a glass or ceramic surface just a short time after adhesion, as for example after approximately 30 minutes.
  • a primer of the invention it is possible, furthermore, for a primer of the invention to be filled with pigments or other functional fillers without thereby reducing its adhesion-promoting effect to any performance relevant extent. Moreover, the rate at which the adhesion-promoting effect begins and develops is hardly impaired by the addition of pigments or other functional fillers. As has been found, this is even the case when the pigments or other functional fillers are present in the primer layer at such a high concentration that the primer layer, when applied in a thickness of around 5-20 ⁇ m to glass, is impervious to light, in other words opaque.
  • the required concentration of the pigments in this case, depending on pigment is between 50 and 200 wt %, based on the total weight of the copolymers.
  • a primer in accordance with the invention and in agreement with DIN EN ISO 4618 is a coating material for producing a primer coating.
  • a primer or coating material is applied to the surface of a substrate, followed by formation of a film through evaporation of a solvent and/or through another chemical or physical curing or film-forming process, after which a further, different substance can be applied to the film thus produced, such as a paint, an ink, an adhesive or an adhesive tape, for example.
  • a fundamental requirement for an adhesion-promoting effect on the part of a primer is firstly that the primer layer adheres effectively to the substrate, the surface of which is also referred to as the base, and secondly that the further, different substance for application to the primer layer produced likewise adheres effectively to said layer.
  • a primer has an optimum adhesion-promoting effect when, in an attempt to peel off the substance applied to the primer, or the adhesive product applied to the primer, the result is cohesive failure within the substance, the adhesive product or the adhesive tape, or when the substrate to which the primer has been applied beforehand is destroyed in this process. If the forces required to peel off the substance, adhesive product, or adhesive tape applied to the primer are higher than if no primer is used, there is an improvement in adhesion or an improvement in the adhesion force. The greater these forces, the stronger the improvement in adhesion or improvement in the adhesion force.
  • a solvent in the sense of the invention is any known liquid which is suitable for dissolving or at least finely dividing the mixture disclosed in the main claim, without entering into an unwanted chemical reaction with the substances according to the invention in this mixture.
  • Preferred solvents of the invention are organic solvents, as for example esters, ketones, and aliphatic and aromatic hydrocarbons.
  • Particularly preferred solvents are those having a boiling point of less than or equal to 100° C.
  • a dispersed mixture in accordance with the invention is a finely divided, homogeneous mixture.
  • the degree of fine division and homogeneity is not strictly defined, but must be sufficient for a coherent layer to be formed after coating, and for the size of the aggregates or agglomerates not dissolved at a molecular level to be sufficiently low that the function of the primer layer as, for example, an adhesion-promoting layer is ensured.
  • the mixture G present in the primer of the invention preferably comprises at least one copolymer obtained by radical copolymerization of the following monomers: vinylcaprolactam and/or vinylpyrrolidone and one or more of the following monomers a) and/or b):
  • the at least one copolymer of the mixture G of the primer of the invention is preferably a pressure sensitive adhesive. More preferably all copolymers present in the mixture G are pressure sensitive adhesives.
  • a pressure sensitive adhesive is understood in accordance with the invention, as is customary within the general usage, as a material which—in particular at room temperature—is permanently tacky and also adhesive. Characteristics of a pressure sensitive adhesive are that it can be applied by pressure to a substrate and remains adhering there, with no further definition of the pressure to be applied or the period of exposure to this pressure. In certain cases, depending on the precise nature of the pressure sensitive adhesive, the temperature, and the atmospheric humidity and also the substrate, a minimal pressure of short duration, which does not go beyond gentle contact for a brief moment, is enough to achieve the adhesion effect, while in other cases a longer-term period of exposure to a high pressure may be necessary.
  • Pressure sensitive adhesives have particular, characteristic viscoelastic properties which result in the permanent tack and adhesiveness.
  • a characteristic of these adhesives is that when they are mechanically deformed, there are processes of viscous flow and there is also development of elastic forces of recovery. The two processes have a certain relationship to one another in terms of their respective proportion, in dependence not only on the precise composition, the structure, and the degree of crosslinking of the pressure sensitive adhesive, but also on the rate and duration of the deformation, and on the temperature.
  • the proportional viscous flow is necessary for the achievement of adhesion. Only the viscous components, brought about by macromolecules with relatively high mobility, permit effective wetting and effective flow onto the substrate where bonding is to take place. A high viscous flow component results in high tack (also referred to as surface stickiness) and hence often also in a high peel adhesion. Highly crosslinked systems, crystalline polymers, or polymers with glasslike solidification lack flowable components and are therefore in general devoid of tack or possess only little tack at least.
  • the proportional elastic forces of recovery are necessary for the attainment of cohesion. They are brought about, for example, by very long-chain macromolecules with a high degree of coiling, and also by physically or chemically crosslinked macromolecules, and they allow the transmission of the forces that act on an adhesive bond. As a result of these forces of recovery, an adhesive bond is able to withstand a long-term load acting on it, in the form of a long-term shearing load, for example, sufficiently over a relatively long time period.
  • G′ storage modulus
  • G′′ loss modulus
  • the variables can be determined with the aid of a rheometer.
  • the material under investigation is exposed in a plate/plate arrangement to a sinusoidally oscillating shearing stress.
  • the deformation is measured as a function of time, and the time offset of this deformation is measured relative to the introduction of the shearing stress. This time offset is referred to as phase angle ⁇ .
  • a substance is considered in general to be a pressure sensitive adhesive, and is defined as being pressure-sensitively adhesive for the purposes of this specification, if at room temperature, presently by definition 23° C., in the deformation frequency range from 10 0 to 10 1 rad/sec, G′ is located at least partly in the range from 10 3 to 10 7 Pa and if G′′ likewise is located at least partly within this range. “Partly” means that at least one section of the G′ curve lies within the window described by the deformation frequency range from 10 0 inclusive up to 10 1 inclusive rad/sec (abscissa) and by the G′ value range from 10 3 inclusive up to 10 7 inclusive Pa (ordinate), and if at least one section of the G′′ curve is likewise located within this window.
  • Pressure sensitive adhesives which comprise vinylcaprolactam and/or vinylpyrrolidone in the copolymer customarily have only average adhesive qualities. It was all the more surprising that in the context of the present invention it has been found that a primer whose pressure sensitive adhesive is a copolymer of the invention having vinylcaprolactam and/or vinylpyrrolidone as monomer components has outstanding adhesion-promoting qualities and produces a very strong bond of adhesive tapes to hydrophilic substrates, especially glass.
  • the copolymer is a pressure sensitive adhesive
  • the monomer mixture of the copolymer comprises only vinylcaprolactam and/or vinylpyrrolidone and also one or more of the monomers a) and/or b), meaning that the copolymer is synthesized only from these monomers, without other copolymerizable monomers being present.
  • a primer based on such a copolymer has particularly good adhesion-promoting qualities. Furthermore, it is possible advantageously to do without the presence of comonomers—especially plasticizing comonomers—and components other than those stated. Thus, for example, it is possible to do entirely without comonomers having cyclic hydrocarbon units.
  • Linear acrylic esters having 2 to 10 C atoms in the alkyl radical are ethyl acrylate, n-propyl acrylate, n-butyl acrylate, n-pentyl acrylate, n-hexyl acrylate, n-heptyl acrylate, n-octyl acrylate, n-nonyl acrylate, n-decyl acrylate.
  • the monomer mixture comprises n-butyl acrylate.
  • Branched noncyclic acrylic esters having from 3 up to and including 12 carbon atoms in the alkyl radical of the alcohol are preferably selected from the group consisting of 2-ethylhexyl acrylate (EHA), 2-propylheptyl acrylate, isooctyl acrylate, isobutyl acrylate, isoamyl acrylate, and isodecyl acrylate.
  • EHA 2-ethylhexyl acrylate
  • 2-propylheptyl acrylate isooctyl acrylate
  • isobutyl acrylate isoamyl acrylate
  • isodecyl acrylate isodecyl acrylate.
  • the monomers b) are selected from the group consisting of 2-ethylhexyl acrylate (EHA), 2-propylheptyl acrylate, and isooctyl acrylate (more precisely: the acrylic esters in which the alcohol component derives from a mixture of primary isooctanols, in other words from those alcohols obtainable from an isoheptene mixture by hydroformylation and subsequent hydrogenation).
  • EHA 2-ethylhexyl acrylate
  • 2-propylheptyl acrylate 2-propylheptyl acrylate
  • isooctyl acrylate more precisely: the acrylic esters in which the alcohol component derives from a mixture of primary isooctanols, in other words from those alcohols obtainable from an isoheptene mixture by hydroformylation and subsequent hydrogenation.
  • the (monomers a) and b)): (vinylcaprolactam+vinylpyrrolidone) weight ratio is preferably from 95:5 to 40:60, more preferably from 85:15 to 50:50, in particular from 80:20 to 60:40, as for example from 75:25 to 65:35.
  • the monomer mixture consists of vinylcaprolactam and/or vinylpyrrolidone and precisely one monomer of variety a), with n-butyl acrylate being selected more preferably as monomer a).
  • vinylcaprolactam is particularly preferred. More particularly, therefore, the monomer mixture consists of vinylcaprolactam and n-butyl acrylate.
  • the n-butyl acrylate:vinylcaprolactam weight ratio is preferably from 95:5 to 50:50, more preferably from 80:20 to 60:40.
  • the monomer mixture may contain up to 10 wt %, based on the total weight of the monomer mixture, of further copolymerizable monomers, in addition to the monomers which are encompassed in any case by the subject matter of the invention.
  • further copolymerizable monomers it is possible, without particular restriction, to use all radically polymerizable, C ⁇ C double bond-containing monomers or monomer mixtures that are known to the skilled person.
  • the further monomers may be selected from the group consisting of the following: methyl acrylate, methyl methacrylate, ethyl methacrylate, benzyl acrylate, benzyl methacrylate, phenyl acrylate, phenyl methacrylate, isobornyl acrylate, isobornyl methacrylate, t-butylphenyl acrylate, t-butylphenyl methacrylate, dodecyl methacrylate, lauryl acrylate, n-undecyl acrylate, stearyl acrylate, tridecyl acrylate, behenyl acrylate, cyclohexyl methacrylate, cyclopentyl methacrylate, phenoxyethyl acrylate, phenoxyethyl methacrylate, 2-butoxyethyl methacrylate, 2-butoxyethyl acrylate, 3,3,5-trimethylcyclo
  • the monomer mixture of the copolymer of the primer of the invention preferably comprises at most 50 wt %, more preferably at most 40 wt %, of vinylcaprolactam and vinylpyrrolidone, based on the total weight of the monomer mixture.
  • the monomer mixture comprises preferably at least 10 wt %, more preferably at least 20 wt %, more particularly at least 30 wt % of vinylcaprolactam and/or vinylpyrrolidone, based on the total weight of the monomer mixture.
  • the monomer mixture comprises preferably at most 1 wt %, more preferably at most 0.1 wt %, based on the total weight of the monomer mixture, of acrylic acid. More particularly the monomer mixture is free from acrylic acid.
  • the concentration of the copolymer or of the entirety of all copolymers of the mixture G, based on the total weight of the primer, is preferably from 1 wt % to 30 wt %, more preferably from 2 wt % to 20 wt %, in particular from 3 wt % to 10 wt %.
  • the radicals R 1 independently of one another are preferably a methyl, ethyl, 2-methoxyethyl or an acetyl radical.
  • the radicals R 3 independently of one another are preferably a methyl, isooctyl, hexadecyl or a cyclohexyl radical.
  • the radical R 2 is preferably an aminoalkyl, glycidyloxyalkyl, vinyl, methacryloyloxymethyl, 3-methacryloyloxypropyl or a phenyl radical, more particularly a 3-glycidyloxy-(n-) propyl or an aminoalkyl radical or a vinyl group.
  • the organofunctional silane of the general structure (1) contains an aminoalkyl radical or a vinyl group.
  • the organofunctional silane or silanes of the general structure (I) is or are selected more particularly from the group consisting of 3-glycidyloxypropyltrimethoxysilane (e.g., GENIOSIL® GF 80, Wacker), 3-glycidyloxypropyltriethoxysilane (e.g., GENIOSIL® GF 82, Wacker), N-cyclohexylaminomethyl-methyldiethoxysilane, N-cyclohexylaminomethyltriethoxysilane, N-phenylaminomethyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-cyclohexyl-3-aminopropyltrimethoxy
  • alkoxy-metal acetylacetonate are metal alkoxide acetylacetonate or metal acetyl acetonate alkoxide.
  • the metal compound may carry further ligands without departing from the concept of the invention.
  • the metal is preferably selected from the group consisting of titanium, aluminum, zirconium, zinc, and iron; more particularly the metal is titanium or zirconium.
  • the metal compound is selected from titanium or zirconium alkoxides.
  • the metal compound is titanium tetraisopropoxide Ti(iPr) 4 .
  • the weight fraction of the entirety of the metal compounds in the mixture G is preferably greater than the weight fraction of the entirety of the organofunctional silanes of the general structure (I).
  • a primer of the invention may comprise further constituents, examples being additives such as other polymers, resins, plasticizers, stabilizers, rheological additives, fillers, pigments, crosslinkers, initiators, catalysts, accelerators, and the like.
  • a water scavenger has preferably been admixed to the primer of the invention during its preparation. More preferably tosyl isocyanate (CAS No. 4083-64-1) was admixed to the primer of the invention during its preparation.
  • the fraction of the water scavenger used is preferably 1 to 15 wt %, more preferably 5 to 10 wt %, based on the entirety of all copolymers of the mixture G.
  • the primer of the invention is preferably free from polymers other than the copolymer(s) of the mixture G, more particularly from chlorinated polyolefins.
  • the primer of the invention advantageously contains no block copolymers of the polystyrene/polydiene or polystyrene/hydrogenated polydiene type.
  • Block copolymers of the polystyrene/polydiene or polystyrene/hydrogenated polydiene type are understood in the sense of this specification to be all polymers whose molecules consist of linked blocks of polystyrene and polydiene units or hydrogenated or part-hydrogenated polydiene units or else comprise such blocks at least in substantial fractions.
  • Typical examples of polydiene units and also hydrogenated or part-hydrogenated polydiene units are polybutadiene, polyisoprene, polymerized ethylene/butylene and ethylene/propylene blocks.
  • block copolymers of the polystyrene/polydiene or polystyrene/hydrogenated polydiene type have the disadvantage, as an additional constituent in the primer of the invention, of impairing the adhesion of the primer to hydrophilic surfaces such as, in particular, glass or ceramic, as compared with a primer of the invention without this additional constituent.
  • the addition of block copolymers of the polystyrene/polydiene or polystyrene/hydrogenated polydiene type to the primer of the invention necessitates a different, less polar solvent or solvent mixture than would be necessary without such addition. More particularly, the addition of toluene or benzine is necessary in order to obtain a homogeneous primer solution. These solvents, however, have a comparatively high boiling point, and so the desire for a rapid drying time of the primer cannot be met using them.
  • the primer of the invention is free from epoxy resins.
  • the primer of the invention preferably comprises one or more fluorescent optical brighteners.
  • One preferred fluorescent optical brightener is 2,5-thiophenediylbis(5-tert-butyl-1,3-benzoxazole), CAS No. 7128-64-5, available commercially under the trade name Tinopal OB®.
  • the sum of the weight fractions of the mixture G and of the solvents in the primer of the invention is preferably at least 80%, more preferably at least 85%, more particularly at least 90%, as for example at least 92%, and very preferably at least 95%.
  • a primer of the invention preferably comprises the following components in the proportions stated, based in each case on the total weight of the primer:
  • a further subject of the invention is the use of a primer of the invention for producing an adhesion-promoting layer, preferably for producing an adhesion-promoting layer comprising pigments and/or other functional fillers, more particularly an adhesion-promoting layer comprising carbon black.
  • a further subject of the invention is a method for producing an adhesion-promoting layer on a substrate, which comprises applying a primer of the invention to a substrate and removing the one or more solvents.
  • Primers of the invention have excellent adhesion to glass in particular, but also to many other hydrophilic surfaces such as ceramic, for example.
  • Adhesive tapes with polar pressure sensitive adhesives more particularly with pressure sensitive adhesives based on copolymers of acrylic esters and acrylic acid, exhibit excellent adhesion to a primer of the invention.
  • the excellent adhesion is manifested by the adhesive tape being predominantly detachable only with destruction, in other words with internal adhesive-tape splitting.
  • the adhesion-promoting effect of a primer of the invention begins, surprisingly, very rapidly.
  • An adhesive tape adhered to the primer layer can frequently no longer be detached without destruction from the primer layer applied to a glass or ceramic surface just a short time after bonding, usually after approximately 30 minutes.
  • peel increase is understood by the skilled person to refer to the increase in bond strength on storage of an adhesive assembly composed of substrate and adhesive tape.
  • Primers of the invention could also be formulated in such a way that an adhesive tape can be detached predominantly only with destruction of the adhesive tape after several weeks of heat-and-humidity storage or cyclical-conditions storage (temperatures from 60° to 90° C. in conjunction with relative humidity of greater than or equal to 80%) of the adhesive assembly, comprising the substrate coated with the primer, and the adhesive tape adhered to said substrate.
  • the adhesion-promoting effect of the primer is not impaired—at least not measurably so—even when color pigments or other functional fillers, especially mineral fillers, are added to the primer.
  • the rate at which the adhesion-promoting effect begins and develops, and the extent of the effect, are also unaffected by the addition of color pigments or other functional fillers, not even when the color pigments or other functional fillers are present in the primer layer at such a high concentration that the primer layer is impervious to light, in other words opaque, when applied at a thickness of around 5-20 ⁇ m to glass.
  • the necessary concentration of the color pigments in this case is between 50 and 200 percent by mass, based on the copolymer, depending on color pigment. Even with this concentration of color pigment or filler in the primer, the adhesion of the adhesive tapes is still good enough for cohesive failure to occur within the adhesive tape in a peel test with adhesive bonds to glass or ceramic, this effect being achieved just 30 minutes after the adhering of the adhesive tape to the primer layer applied to the glass or ceramic surface.
  • the primer of the invention may be furnished with defined functionalities, if functional fillers are to be used.
  • the primer may not only be colored, as described, if color pigments such as carbon black or titanium dioxide, for example, are added; instead, the primer, furthermore, may also be made electrically or thermally conductive, if metal particles, for example, are added.
  • the pH of the primer may also be adjusted through the choice of the filler, and by this means, for example, an antibacterial effect can be produced by using calcium oxide.
  • Fillers with rheological activity as well, such as fumed silicas, for example, may be used, and so relatively thick, dimensionally stable primer layers, for example, can also be produced. It is possible, furthermore, to lower the costs of the primer without a measurable impairment in performance capacity, by means of a high fraction of inexpensive mineral fillers, such as chalk, for example.
  • An adhesion-promoting layer is produced with the primer of the invention in a known way, specifically by application of the primer to a substrate first of all. Thereafter the solvent or solvents is or are caused to evaporate, after which the adhesive tape can be applied.
  • the time between application/evaporation of the solvent and application of the adhesive tape may be just a few minutes, or else several days or weeks.
  • the pressure-sensitive adhesion of the copolymers in the primer was characterized by determination of the storage modulus G′ and loss modulus G′′ by means of dynamic mechanical analysis (DMA).
  • the measurements were made using the DSR 200 N shear stress-controlled rheometer from Rheometric Scientific in an oscillation test with a sinusoidally oscillating shearing stress in a plate/plate arrangement.
  • the storage modulus G′ and the loss modulus G′′ were determined in a frequency sweep from 10 ⁇ 1 to 10 2 rad/sec at a temperature of 23° C.
  • G′ and G′′ are defined as follows:
  • the unit is rad/sec.
  • the thickness of the pressure-sensitive adhesive (PSA) copolymer samples measured was always between 0.9 and 1.1 mm (1+/ ⁇ 0.1 mm).
  • the PSA copolymer samples were produced by coating out the copolymers described later on below on a double-sidedly siliconized polyester film (release liner), evaporating the solvent at 70° C., and piling up the resulting 100 ⁇ m coats on one another until a thickness of about 1 mm was reached.
  • the sample diameter was 25 mm in each case.
  • Preliminary tension was applied with a load of 3 N. For all of the measurements, the stress of the sample specimens was 2500 Pa.
  • the peel adhesion was determined in accordance with PSTC-101 at room temperature.
  • the primer was first applied thinly to the substrate. This was done by brush application of the primer to the substrate.
  • the adhesive strip under measurement (the adhesive tape) was applied (adhered) to the substrate now bearing the primer in a layer thickness of approximately 1 ⁇ m to 10 ⁇ m.
  • a strip of the adhesive tape in a defined width (standard: 20 mm) was bonded to the primer-coated substrate, with dimensions of 50 mm ⁇ 125 mm ⁇ 1.1 mm, by rolling over it ten times with a 5 kg steel roller.
  • the time between the last rollover of the adhesive tape and the peel removal was as follows: a) 30 minutes; b) 3 days.
  • the peel angle was 90° in each case and the peel rate 300 mm/min.
  • the force required for peel removal is the peel adhesion, which is reported in the unit N/cm and thus relates to a standardized adhesive tape width of 1 cm.
  • the nature of adhesive bond failure was ascertained.
  • the adhesive strips measured were reinforced on the reverse with a polyester film that was 23 ⁇ m thick and had undergone incipient etching with trichloroacetic acid. All measurements were conducted in a controlled-climate space at 23° C. and 50% relative humidity.
  • the assemblies comprising the substrate coated with the primer of the invention and the adhesive tape adhered to that substrate were subjected to storage under selected climatic conditions, in order to determine the climatic robustness of the bond.
  • the samples which were reinforced on the reverse with a polyester film having a thickness of 23 ⁇ m and having been incipiently etched with trichloroacetic acid, were subjected to the peel adhesion test with a peel angle of 90° in each case and with a peel rate of 300 mm/min, in a controlled-climate space at 23° C. and 50% relative humidity.
  • the light transmittance was measured using the UVIKON 923 UV/VIS spectrometer from Kontron, in the wavelength range from 190 to 850 nm.
  • the static glass transition temperature is determined via differential scanning calorimetry in accordance with DIN 53765.
  • the figures for the glass transition temperature T g refer to the glass transformation temperature value T g in accordance with DIN 53765:1994-03, unless indicated otherwise in any specific case.
  • Heating curves run with a heating rate of 10 K/min. The specimens are measured in Al crucibles with a perforated lid under a nitrogen atmosphere. Evaluation takes place on the second heating curve. A glass transition temperature is evident as an inflection point on the thermogram.
  • the preliminary column used was a PSS-SDV, 5 ⁇ m, 10 3 ⁇ (10 ⁇ 7 m), ID 8.0 mm ⁇ 50 mm. Separation took place using the columns PSS-SDV, 5 ⁇ m, 10 3 ⁇ , (10 ⁇ 7 m), 10 5 ⁇ (10 ⁇ 5 m), and 10 6 ⁇ (10 ⁇ 4 m), each with ID 8.0 mm ⁇ 300 mm.
  • the sample concentration was 4 g/l, the flow rate 1.0 ml per minute. Measurement took place against PMMA standards.
  • the solids content is a measure of the fraction of unvaporizable constituents in a polymer solution. It is determined gravimetrically, with the solution being weighed, the vaporizable fractions then being evaporated off in a drying cabinet at 120° C. for 2 hours, and the residue being weighed again.
  • the K value is a measure of the average molecular size of high-polymer compounds.
  • one percent strength (1 g/100 ml) toluenic polymer solutions were prepared and their kinematic viscosities were determined by means of a Vogel-Ossag viscometer. Standardization to the viscosity of toluene gives the relative viscosity, from which the K value can be calculated by the method of Fikentscher (Polymer 8/1967, 381 ff.).
  • the substrates used (to which the primer was applied first of all, followed by the adhesive tape being adhered thereto) were as follows:
  • the adhesive tapes (test adhesive tapes) with which the primer was tested were based on polyacrylate PSAs. These polyacrylate PSAs were prepared using the following raw materials:
  • the expansion capacity of the microballoons can be described through the determination of the TMA density [kg/m 3 ] (Stare Thermal Analysis System from Mettler Toledo; heating rate 20° C./min).
  • the TMA density here is the minimum achievable density at a defined temperature T max under atmospheric pressure before the microballoons collapse.
  • the softening point of the resins is determined in accordance with DIN ISO 4625.
  • An example polyacrylate PSA 1 for producing the test adhesive tape 1 was prepared as follows: A reactor conventional for radical polymerizations was charged with 54.4 kg of 2-ethylhexyl acrylate, 20.0 kg of methyl acrylate, 5.6 kg of acrylic acid, and 53.3 kg of acetone/isopropanol (94:6). After nitrogen gas had been passed through the reactor for 45 minutes, with stirring, the reactor was heated to 58° C. and 40 g of Vazo 67, in solution in 400 g of acetone, were added. Thereafter the external heating bath was heated to 75° C. and the reaction was carried out constantly at this external temperature. After 1 hour a further 40 g of Vazo 67, in solution in 400 g of acetone, were added, and after 4 hours the batch was diluted with 10 kg of acetone/isopropanol mixture (94:6).
  • This base polymer was melted in a feeder-extruder (single-screw conveying extruder from TROESTER GmbH & Co. KG, Germany) and in the form of a polymer melt was conveyed with said extruder, via a heatable hose, into a planetary roller extruder from Entex (Bochum).
  • the melted resin Dertophene T 110 was then added via a metering port, to give the melt a resin concentration of 28.3 mass percent.
  • the crosslinker Polypox R16 was added. Its concentration in the melt was 0.14 mass percent. All components were mixed to give a homogeneous polymer melt.
  • the polymer melt was transferred to a twin-screw extruder (from Berstorff). There the accelerator Epikure 925 was added. Its concentration in the melt was 0.14 mass percent. The entire polymer mixture was then freed from all gas inclusions in a vacuum dome under a pressure of 175 mbar. After the vacuum zone, the microballoons were metered in and were incorporated homogeneously into the polymer mixture by means of a mixing element. Their concentration in the melt was 0.7 mass percent. The resulting melt mixture was transferred into a die.
  • the incorporated microballoons underwent expansion, with the drop in pressure producing shear-free cooling of the polymer composition.
  • the wound film is test adhesive tape 1.
  • An example polyacrylate PSA 2A for producing the middle layer of the three layer test adhesive tape 2 was prepared as follows:
  • a reactor conventional for radical polymerizations was charged with 30.0 kg of 2-ethylhexyl acrylate, 67.0 kg of butyl acrylate, 3.0 kg of acrylic acid, and 66.7 kg of acetone/isopropanol (96:4). After nitrogen gas had been passed through the reactor for 45 minutes, with stirring, the reactor was heated to 58° C. and 50 g of Vazo 67, in solution in 500 g of acetone, were added. Thereafter the external heating bath was heated to 70° C. and the reaction was carried out constantly at this external temperature.
  • This base polymer was melted in a feeder-extruder (single-screw conveying extruder from TROESTER GmbH & Co. KG, Germany) and in the form of a polymer melt was conveyed with said extruder, via a heatable hose, into a planetary roller extruder from Entex (Bochum). Then the crosslinker Polypox R16 was added via a metering port. Its concentration in the melt was 0.22 mass percent. All components were mixed to give a homogeneous polymer melt.
  • the polymer melt was transferred to a twin-screw extruder (from Berstorff). There the accelerator Epikure 925 was added. Its concentration in the melt was 0.14 mass percent. The entire polymer mixture was then freed from all gas inclusions in a vacuum dome under a pressure of 175 mbar. After the vacuum zone, the microballoons were metered in and were incorporated homogeneously into the polymer mixture by means of a mixing element. Their concentration in the melt was 2.0 mass percent. The resulting melt mixture was transferred into a die.
  • the incorporated microballoons underwent expansion, with the drop in pressure producing shear-free cooling of the polymer composition.
  • the wound film was stored at room temperature for a day before further processing (see below).
  • An example polyacrylate PSA 2B for producing the two outer layers of the three-layer test adhesive tape 2 was prepared as follows:
  • a 100 l glass reactor conventional for radical polymerizations was charged with 4.8 kg of acrylic acid, 11.6 kg of butyl acrylate, 23.6 kg of 2-ethylhexyl acrylate, and 26.7 kg of acetone/special-boiling-point spirit 60/95 (1:1). After nitrogen gas had been passed through the reactor for 45 minutes, with stirring, the reactor was heated to 58° C. and 30 g of AIBN were added. Thereafter the external heating bath was heated to 75° C. and the reaction was carried out constantly at this external temperature. After a reaction time of 1 hour, a further 30 g of AIBN were added.
  • a film of the polyacrylate PSA 2B was laminated onto both sides of the foamed film of polyacrylate PSA 2A.
  • the respective surface of the film of polyacrylate PSA 2A to be laminated was subjected to air corona pretreatment with a corona dose of 35 Wmin/m 2 .
  • the double-sidedly siliconized release film of the foamed polyacrylate PSA 2A was lined.
  • one of the double-sidedly siliconized release films of the two foamed polyacrylate PSAs 2B was lined as well.
  • the 3-layer assembly composed of polyacrylate PSA 2B/polyacrylate PSA 2A/polyacrylate PSA 2B was wound up and stored at room temperature for four weeks before being further used for primer testing.
  • the wound assembly is test adhesive tape 2.
  • Polyacrylate PSAs for use as a constituent in the primer of the invention were prepared as follows:
  • a 100 l glass reactor conventional for radical polymerizations was charged with 12.0 kg of N-vinylcaprolactam, 28.0 kg of butyl acrylate, and 26.7 kg of acetone/special-boiling-point spirit 60/95 (1:1). After nitrogen gas had been passed through the reactor for 45 minutes, with stirring, the reactor was heated to 58° C. and 30 g of AIBN were added. Thereafter the external heating bath was heated to 75° C. and the reaction was carried out constantly at this external temperature. After a reaction time of 1 hour, a further 30 g of AIBN were added. After 4 hours and again after 8 hours, dilution took place with 10.0 kg of acetone/special-boiling-point spirit 60/95 (1:1) mixture each time.
  • a 100 l glass reactor conventional for radical polymerizations was charged with 8.0 kg of N-vinylcaprolactam, 32.0 kg of 2-ethylhexyl acrylate, and 26.7 kg of acetone/special-boiling-point spirit 60/95 (1:1). After nitrogen gas had been passed through the reactor for 45 minutes, with stirring, the reactor was heated to 58° C. and 30 g of AIBN were added. Thereafter the external heating bath was heated to 75° C. and the reaction was carried out constantly at this external temperature. After a reaction time of 1 hour, a further 30 g of AIBN were added.
  • a 100 l glass reactor conventional for radical polymerizations was charged with 8.0 kg of N-vinyl-2-pyrrolidone, 32 kg of butyl acrylate, and 26.7 kg of acetone/special-boiling-point spirit 60/95 (1:1). After nitrogen gas had been passed through the reactor for 45 minutes, with stirring, the reactor was heated to 58° C. and 30 g of AIBN were added. Thereafter the external heating bath was heated to 75° C. and the reaction was carried out constantly at this external temperature. After a reaction time of 1 hour, a further 30 g of AIBN were added. After 4 hours and again after 8 hours, dilution took place with 10.0 kg of acetone/special-boiling-point spirit 60/95 (1:1) mixture each time.
  • a 100 l glass reactor conventional for radical polymerizations was charged with 15.4 kg of butyl acrylate, 24.4 kg of 2-ethylhexyl acrylate, and 26.7 kg of acetone/special-boiling-point spirit 60/95 (1:1). After nitrogen gas had been passed through the reactor for 45 minutes, with stirring, the reactor was heated to 58° C. and 30 g of AIBN were added. Thereafter the external heating bath was heated to 75° C. and the reaction was carried out constantly at this external temperature. After a reaction time of 1 hour, a further 30 g of AIBN were added.
  • Primer PSAs 1 to 4 were briefly characterized by DMA measurements.
  • the following solvent was used for preparing the primers of the invention:
  • auxiliaries were also used as auxiliaries:
  • the raw materials/components specified in the examples were mixed with a laboratory agitator from IKA®, using a propeller stirrer, for 20 minutes.
  • the stated pigments and rheological additives in all examples, in order to produce a finely particulate, opaque primer layer, were incorporated using the Ultra-Turrax® T50 laboratory dissolver from IKA®, operating according to the rotor-stator principle, by first dispersing the pigment and, where appropriate, the other rheological additives into the initially prepared mixture of primer PSA and ethyl acetate, and only then mixing in the remaining raw materials/components.
  • the Ultra-Turrax® T50 was operated using a rotary speed of 7000 revolutions per minute.
  • the remaining raw materials/components were admixed with the IKA® laboratory agitator, using a propeller stirrer.
  • compositions of the primers comprising pigments and, where appropriate, rheological additives, while retaining the fundamental primer composition from example 1, were as follows:
  • a layer of this primer 8 ⁇ m thick on glass was opaque.
  • the transmittance in the wavelength range from 300 nm to 650 nm was 0%.
  • the primer was tested in the same way with the same test adhesive tapes as the pigment-free primer from example 1, giving the same results—that is, in all cases the test adhesive tape underwent cohesive splitting.
  • a layer of this primer 10 ⁇ m thick on glass was opaque.
  • the transmittance in the wavelength range from 300 nm to 650 nm was 0%.
  • the primer was tested in the same way with the same test adhesive tapes as the color pigment-free primer from example 1, giving the same results—that is, in all cases the test adhesive tape underwent cohesive splitting.
  • compositions of the primers comprising color pigments and, where appropriate, rheological additives, while retaining the fundamental primer composition from example 2, were as follows:
  • a layer of this primer 8 ⁇ m thick on glass was opaque.
  • the transmittance in the wavelength range from 300 nm to 650 nm was 0%.
  • the primer was tested in the same way with the same test adhesive tapes as the color pigment-free primer from example 2, giving the same results—that is, in all cases the test adhesive tape underwent cohesive splitting.
  • a layer of this primer 10 ⁇ m thick on glass was opaque.
  • the transmittance in the wavelength range from 300 nm to 650 nm was 0%.
  • the primer was tested in the same way with the same test adhesive tapes as the color pigment-free primer from example 2, giving the same results—that is, in all cases the test adhesive tape underwent cohesive splitting.
  • compositions of the primers comprising color pigments and, where appropriate, rheological additives, while retaining the fundamental primer composition from example 3, were as follows:
  • a layer of this primer 8 ⁇ m thick on glass was opaque.
  • the transmittance in the wavelength range from 300 nm to 650 nm was 0%.
  • the primer was tested in the same way with the same test adhesive tapes as the color pigment-free primer from example 3, giving the same results—that is, in all cases the test adhesive tape underwent cohesive splitting.
  • a layer of this primer 10 ⁇ m thick on glass was opaque.
  • the transmittance in the wavelength range from 300 nm to 650 nm was 0%.
  • the primer was tested in the same way with the same test adhesive tapes as the color pigment-free primer from example 3, giving the same results—that is, in all cases the test adhesive tape underwent cohesive splitting.
  • composition of the primer comprising color pigments while retaining the fundamental primer composition from example 4, was as follows:
  • a layer of this primer 8 ⁇ m thick on glass was opaque.
  • the transmittance in the wavelength range from 300 nm to 650 nm was 0%.
  • the primer was tested in the same way with the same test adhesive tapes as the color pigment-free primer from example 4, giving the same results—that is, in all cases the test adhesive tape underwent cohesive splitting.
  • composition of the primer comprising color pigments while retaining the fundamental primer composition from example 5, was as follows:
  • a layer of this primer 8 ⁇ m thick on glass was opaque.
  • the transmittance in the wavelength range from 300 nm to 650 nm was 0%.
  • the primer was tested in the same way with the same test adhesive tapes as the color pigment-free primer from example 5, giving the same results—that is, in all cases the test adhesive tape underwent cohesive splitting.
  • composition of the primer comprising color pigments while retaining the fundamental primer composition from example 6, was as follows:
  • a layer of this primer 8 ⁇ m thick on glass was opaque.
  • the transmittance in the wavelength range from 300 nm to 650 nm was 0%.
  • the primer was tested in the same way with the same test adhesive tapes as the color pigment-free primer from example 6, giving the same results—that is, in all cases the test adhesive tape underwent cohesive splitting.
  • composition of the primer comprising color pigments while retaining the fundamental primer composition from example 7, was as follows:
  • a layer of this primer 8 ⁇ m thick on glass was opaque.
  • the transmittance in the wavelength range from 300 nm to 650 nm was 0%.
  • the primer was tested in the same way with the same test adhesive tapes as the color pigment-free primer from example 7, giving the same results—that is, in all cases the test adhesive tape underwent cohesive splitting.
  • the fluorescent optical brightener in a functional concentration in all examples without any deterioration in the adhesion-promoting effect.
  • This functional concentration was selected at 1.5 mass percent, based on the solvent-free fraction of the primer.
  • the primer was tested in the following way with the test adhesive tapes, giving the following results:
  • the primer was tested in the following way with the test adhesive tapes, giving the following results:
  • the primer was tested in the following way with the test adhesive tapes, giving the following results:

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DE102014208814.3A DE102014208814A1 (de) 2014-05-09 2014-05-09 Primer zur Verbesserung der Adhäsion von Klebebändern auf hydrophilen Oberflächen
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PCT/EP2015/058495 WO2015169575A1 (fr) 2014-05-09 2015-04-20 Primaire pour améliorer l'adhérence de bandes adhésives à surfaces hydrophiles

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WO2024257046A1 (fr) 2023-06-15 2024-12-19 3M Innovative Properties Company Composition d'apprêt, système adhésif et processus associés
US12187929B2 (en) 2018-02-09 2025-01-07 3M Innovative Properties Company Film-initiated cure of structural adhesive film
WO2025037281A1 (fr) 2023-08-17 2025-02-20 3M Innovative Properties Company Composition conductrice, système adhésif de décollement électrique et procédés associés
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WO2015169575A1 (fr) 2015-11-12
DE102014208814A1 (de) 2015-11-12
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CN106459714B (zh) 2019-08-09
JP2017519093A (ja) 2017-07-13
EP3140344A1 (fr) 2017-03-15

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